Identification of the flavin monooxygenase responsible for ipso substitution of alkyl and alkoxyphenols in Sphingomonas sp. TTNP3 and Sphingobium xenophagum Bayram

Applied Microbiology and Biotechnology

Volumn 94, Issue 1, 2012, Pages 261-272

  Porter, A W ^a,b   Campbell, B R ^a,c   Kolvenbach, B A ^d   Corvini, P F X ^d   Benndorf, D ^e   Rivera Cancel, G ^a   Hay, A G ^a,f  

^a WEILL CORNELL MEDICAL COLLEGE   (United States)

^b Rutgers University   (United States)

^c Medical Instill Technologies Inc   (United States)

^d UNIVERSITY OF APPLIED SCIENCES AND ARTS NORTHWESTERN SWITZERLAND   (Switzerland)

^e OTTO VON GUERICKE UNIVERSITY   (Germany)

^f NONE   (United States)

Author keywords

Alkylphenol biodegradation; Ipso substitution; Octylphenol; Octylphenol monooxygenase

Indexed keywords

ALKYL PHENOLS; COMPLEMENTATION; FOUR AMINO ACIDS; IN-SILICO MODELS; MONOOXYGENASES; NONYLPHENOLS; OCTYLPHENOLS; PROTEIN SEQUENCES; SEQUENCE ANALYSIS; SOUTHERN BLOT ANALYSIS; SPHINGOBIUM; SPHINGOMONAS SP; SUBSTITUTION MECHANISMS; SUBSTRATE BINDING; SUBSTRATE SPECIFICITY; TWO-DIMENSIONAL GEL ELECTROPHORESIS; TYPE II; WILD TYPES;

AMINO ACIDS; BIODEGRADATION; DEGRADATION; ELECTROPHORESIS; ENCODING (SYMBOLS); KETONES; PHENOLS;

SUBSTRATES;

NONYLPHENOL; QUERCETIN; UNSPECIFIC MONOOXYGENASE;

AMINO ACID; BACTERIUM; ELECTROKINESIS; ENZYME ACTIVITY; GEL; GENE EXPRESSION; IMMUNOASSAY; PHENOL; SUBSTRATE;

AMINO ACID SEQUENCE; ARTICLE; BACTERIAL STRAIN; BACTERIUM; CONTROLLED STUDY; NONHUMAN; POLYMERASE CHAIN REACTION; PROTEIN EXPRESSION; SEQUENCE ANALYSIS; SOUTHERN BLOTTING; SPHINGOBIUM XENOPHAGUM; SPHINGOMONAS; TWO DIMENSIONAL GEL ELECTROPHORESIS;

BACTERIAL PROTEINS; BIODEGRADATION, ENVIRONMENTAL; MIXED FUNCTION OXYGENASES; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; PHENOLS; SPHINGOMONADACEAE; SPHINGOMONAS;

SPHINGOBIUM; SPHINGOMONAS SP.;

EID: 84858443053     PISSN: 01757598     EISSN: 14320614     Source Type: Journal    
DOI: 10.1007/s00253-011-3621-8     Document Type: Article

References (24)

1. B Ajithkumar VP Ajithkumar R Iriye 2003 Degradation of 4-amylphenol and 4-hexylphenol by a new activated sludge isolate of Pseudomonas veronii and proposal for a new subspecies status Res Microbiol 154 17 23 10.1016/S0923-2508(02)00009-8 1:CAS:528:DC%2BD3sXptFekug%3D%3D (Pubitemid 36165162)
2. SF Altschul TL Madden AA Schäffer J Zhang Z Zhang W Miller DJ Lipman 1997 Gapped BLAST and PSI-BLAST: a new generation of protein database search programs Nucleic Acids Res 25 3389 3402 10.1093/nar/25.17.3389 1:CAS:528:DyaK2sXlvFyhu7w%3D (Pubitemid 27359211)
3. PFX Corvini R Vinken G Hommes M Mundt J Hollender RJW Meesters HF Schröder B Schmidt 2004 Microbial degradation of a single branched isomer of nonylphenol by Sphingomonas TTNP3 Water Sci Technol 50 189 194 1:CAS:528:DC%2BD2cXovF2rurY%3D
4. PF-X Corvini M Elend J Hollender R Ji A Preiss R Vinken A Schäffer 2005 Metabolism of a nonylphenol isomer by Sphingomonas sp. strain TTNP3 Environ Chem Lett 2 185 189 10.1007/s10311-004-0094-3 1:CAS:528:DC%2BD2MXksFKjs74%3D (Pubitemid 40468399)
5. PF-X Corvini J Hollender R Ji S Schumacher J Prell G Hommes U Priefer R Vinken A Schäffer 2006 The degradation of α-quaternary nonylphenol isomers by Sphingomonas sp. strain TTNP3 involves a type II ipso-substitution mechanism Appl Microbiol Biotechnol 70 114 122 10.1007/s00253-005-0080-0 1:CAS:528:DC%2BD28Xhtlegs7Y%3D (Pubitemid 43234537)
6. FLP Gabriel W Giger K Guenther H-PE Kohler 2005 Differential degradation of nonylphenol isomers by Sphingomonas xenophaga Bayram Appl Environ Microbiol 71 1123 1129 10.1128/AEM.71.3.1123-1129.2005 1:CAS:528:DC%2BD2MXisVOjurk%3D (Pubitemid 40396645)
7. FLP Gabriel A Heidlberger D Rentsch W Giger K Guenther H-PE Kohler 2005 A novel metabolic pathway for degradation of 4-nonylphenol environmental contaminants by Sphingomonas xenophaga Bayram. Ipso-hydroxylation and intramolecular rearrangement. J Biol Chem 280 15526 15533 10.1074/jbc.M413446200 1:CAS:528:DC%2BD2MXjtlejurc%3D (Pubitemid 40616668)
8. FLP Gabriel M Cyris W Giger H-PE Kohler 2007 ipso-Substitution: a general biochemical and biodegradation mechanism to cleave α-quaternary alkylphenols and bisphenol A Chem Biodivers 4 2123 2137 10.1002/cbdv.200790170 1:CAS:528:DC%2BD2sXhtFelsr3P (Pubitemid 47527664)
9. FLP Gabriel M Cyris N Jonkers W Giger K Guenther H-PE Kohler 2007 Elucidation of the ipso-substitution mechanism for side-chain cleavage of α-quaternary 4-nonylphenols and 4-t-butoxyphenol in Sphingobium xenophagum Bayram Appl Environ Microbiol 73 3320 3326 10.1128/AEM.02994-06 1:CAS:528:DC%2BD2sXlslSnu7Y%3D (Pubitemid 46834984)
10. T Hiromoto S Fujiwara K Hosokawa H Yamaguchi 2006 Crystal structure of 3-hydroxybenzoate hydroxylase from Comamonas testosteroni has a large tunnel for substrate and oxygen access to the active site J Mol Biol 364 878 896 10.1016/j.jmb.2006.09.031 1:CAS:528:DC%2BD28Xht1eqtbfN (Pubitemid 44765035)
11. JJ Jeong JH Kim C-K Kim I Hwang K Lee 2003 3- and 4-alkylphenol degradation pathway in Pseudomonas sp. strain KL28: genetic organization of the lap gene cluster and substrate specificities of phenol hydroxylase and catechol 2,3-dioxygenase Microbiology 149 3265 3277 10.1099/mic.0.26628-0 1:CAS:528:DC%2BD3sXpsFagtLk%3D (Pubitemid 37442009)
12. B Kolvenbach N Schlaich Z Raoui J Prell S Zühlke A Schäffer FP Guengerich PFX Corvini 2007 Degradation pathway of bisphenol A - Does ipso-substitution apply to phenols para-substituted by a quaternary C alpha structure? Appl Environ Microbiol 73 4776 4784 10.1128/AEM.00329-07 1:CAS:528:DC%2BD2sXptVyht7Y%3D (Pubitemid 47237225)
13. Kovach ME, Elzer PH, Hill DS, Robertson GT, Farris MA, R. Martin Roop I, and Peterson KM (1995) Four new derivatives of the broad-host-range cloning vector pBBR1MCS, carrying different antibiotic-resistance cassettes. Gene 166
14. OH Lowry NJ Rosebrough AL Farr RJ Randall 1951 Protein measurement with the Folin-Phenol reagents J Biol Chem 193 265 275 1:CAS:528:DyaG38XhsVyrsw%3D%3D
15. MV McCullar V Brenner RH Adams DD Focht 1994 Construction of a novel polychlorinated biphenyl-degrading bacterium: utilization of 3,4′-dichlorobiphenyl by Pseudomonas acidovorans M3GY Appl Environ Microbiol 60 3833 3839 1:CAS:528:DyaK2cXmt1eqsL0%3D (Pubitemid 24298881)
16. T Ohe T Mashino M Hirobe 1994 Novel metabolic pathway of arylethers by cytochrome P450: cleavage of the oxygen-aromatic ring bond accompanying ipso-substitution by the oxygen atom of the active species in cytochrome P450 models and cytochrome P450 Arch Biochem Biophys 310 402 409 10.1006/abbi.1994. 1185 1:CAS:528:DyaK2cXltVWgu7k%3D
17. T Ohe T Mashino M Hirobe 1997 Substituent elimination from p-substituted phenols by cytochrome P450 ipso-substitution by the oxygen atom of the active species Drug Metab Dispos 25 116 122 1:CAS:528:DyaK2sXmtlymtw%3D%3D (Pubitemid 27045142)
18. AW Porter AG Hay 2007 Identification of opdA, a gene involved in the biodegradation of the endocrine disrupter octylphenol Appl Environ Microbiol 73 7373 7379 10.1128/AEM.01478-07 1:CAS:528:DC%2BD1cXnsFyhtQ%3D%3D (Pubitemid 350196689)
19. A Sali L Potterton F Yuan H van Vlijmen M Karplus 1995 Evaluation of comparative protein modelling by MODELLER Proteins 23 318 326 10.1002/prot.340230306 1:CAS:528:DyaK2MXpslOqu70%3D
20. PM Santos D Benndorf I Sá-Correia 2004 Insights into Pseudomonas putida KT2440 response to phenol-induced stress by quantitative proteomics Proteomics 4 2640 2652 10.1002/pmic.200300793 1:CAS:528:DC%2BD2cXns1OrsLg%3D (Pubitemid 39202166)
21. J Soding A Biegert AN Lupas 2005 The HHpred interactive server for protein homology detection and structure prediction Nucleic Acids Res 33 W244 W248 10.1093/nar/gki408 (Pubitemid 44529917)
22. M Takeo SK Prabu C Kitamura M Hirai H Takahashi D-I Kato S Negoro 2006 Characterization of alkylphenol degradation gene cluster in Pseudomonas putida MT4 and evidence of oxidation of alkylphenols and alkylcatechols with medium-length alkyl chains J Biosci Bioeng 102 352 361 10.1263/jbb.102.352 1:CAS:528:DC%2BD28Xhtlemsr3O (Pubitemid 44751636)
23. T Toyama N Momotani Y Ogata Y Miyamori D Inoue K Sei K Mori S Kikuchi M Ike 2010 Isolation and Characterization of 4-tert-Butylphenol-Utilizing Sphingobium fuliginis Strains from Phragmites australis rhizosphere sediment Appl Environ Microbiol 76 6733 6740 10.1128/AEM.00258-10 1:CAS:528: DC%2BC3cXhsVKks7%2FL
24. TF Wheeler JR Heim MR LaTorre AB Janes 1997 Mass spectral characterization of p-nonylphenol isomers using high-resolution capillary GC-MS J Chromatogr Sci 35 19 30 1:CAS:528:DyaK2sXit1yluw%3D%3D (Pubitemid 127477125)